DE1255484B - Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer - Google Patents

Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer

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Publication number
DE1255484B
DE1255484B DEA48186A DEA0048186A DE1255484B DE 1255484 B DE1255484 B DE 1255484B DE A48186 A DEA48186 A DE A48186A DE A0048186 A DEA0048186 A DE A0048186A DE 1255484 B DE1255484 B DE 1255484B
Authority
DE
Germany
Prior art keywords
silver salt
light
silver
photosensitive
sensitive
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEA48186A
Other languages
German (de)
Inventor
Dr Edith Weyde
Dr Anita Von Koenig
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to DEA46854A priority Critical patent/DE1214083B/en
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Priority to DEA48186A priority patent/DE1255484B/en
Priority to US472308A priority patent/US3330663A/en
Priority to CH1028065A priority patent/CH458056A/en
Priority to NL6510643A priority patent/NL6510643A/xx
Priority to DK416665AA priority patent/DK113969B/en
Priority to SE10616/65A priority patent/SE310120B/xx
Priority to GB34819/65A priority patent/GB1111492A/en
Priority to FR28394A priority patent/FR1443002A/en
Priority to AT752065A priority patent/AT259366B/en
Priority to BE668340D priority patent/BE668340A/xx
Publication of DE1255484B publication Critical patent/DE1255484B/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/36—Sulfur atoms
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/28—Sulfur atoms
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/58—Two sulfur atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
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    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
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    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
    • G03C1/498—Photothermographic systems, e.g. dry silver

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Description

DEUTSCHES PATENTAMTGERMAN PATENT OFFICE AUSLEGESCHRIFTEDITORIAL

DeutscheKI.: 57 b -8/01 DeutscheKI .: 57 b -8/01

Nummer: 1 255 484Number: 1 255 484

Aktenzeichen: A 48186IX a/57 bFile number: A 48186IX a / 57 b

1255484 Anmeldetag: 21. Januar 1965 1255484 filing date: January 21, 1965

Auslegetag: 30. November 1967Open date: November 30, 1967

Gegenstand des Hauptpatentes ist ein lichtempfindliches photographisches Material mit mindestens einer lichtempfindlichen Silbersalzemulsionsschicht, wobei diese Schicht ein Silbersalz der Thioglykolsäure oder deren Derivaten als lichtempfindliche Verbindung enthält.The main patent is a light-sensitive photographic material with at least a photosensitive silver salt emulsion layer, which layer is a silver salt of Contains thioglycolic acid or its derivatives as a photosensitive compound.

Bei der Weiterbearbeitung des im Hauptpatent beschriebenen Materials wurde gefunden, daß für den gleichen Zweck auch Silbersalze höherer Thiocarbonsäuren mit einer Alkylenkette zwischen der Carboxylgruppe und der Thiogruppierung, die mindestens zwei Kettenglieder enthält, geeignet sind. Brauchbar sind Verbindungen der folgenden allgemeinen FormelIn the further processing of the material described in the main patent, it was found that for the same purpose also silver salts of higher thiocarboxylic acids with an alkylene chain between the Carboxyl group and the thio group, which contains at least two chain links, are suitable. Compounds of the following general formula are useful

- Ri-(S)n-X-COOAg- Ri- (S) n -X-COOAg

worin bedeutet:where means:

Lichtempfindliches photographisches Material
mit mindestens einer lichtempfindlichen
SilbersalzemulsionsschichtPhotographic light sensitive material
with at least one light-sensitive
Silver salt emulsion layer

Zusatz zum Patent: 1 214 083Addendum to the patent: 1 214 083

Anmelder:Applicant:

Agfa-Gevaert Aktiengesellschaft,
Leverkusen, Kaiser-Wilhelm-Allee 24Agfa-Gevaert Aktiengesellschaft,
Leverkusen, Kaiser-Wilhelm-Allee 24

« = 1 oder 2,«= 1 or 2,

R1 = Wasserstoff nur bei η = 1, Alkyl, vorzugsweise bis 18 C-Atomen, Aryl, wie Phenyl oder Naphthyl, vorzugsweise Phenyl, oder heterocyclische Ringe, wie Diazole, Oxazole, Triazole, Thiadiazole, Oxdiazole, Tetrazole, Azaindene, vorzugsweise Tetra- oder Pentaazaindene, Benzthiazole, Naphthothiazole, Benzoxazole, Naphthoxazole, Pyridine, Chinoline, Pyrimidine, Chinoxyline, Chinazoline, wobei diese Reste ihrerseits substituiert sein können, beispielsweise durch Alkyl, vorzugsweise bis zu 18 C-Atomen, Aryl, wie Phenyl oder Naphthyl, Hydroxyl, Alkoxy, Amino, oder alkyl-, acyl- oder arylsubstituierte Aminogruppen, Mercapto-, substituierte Mercaptogruppen, Halogen, Sulfo- oder Carboxylgruppen, R 1 = hydrogen only when η = 1, alkyl, preferably up to 18 carbon atoms, aryl, such as phenyl or naphthyl, preferably phenyl, or heterocyclic rings, such as diazoles, oxazoles, triazoles, thiadiazoles, oxdiazoles, tetrazoles, azaindenes, preferably tetra - Or pentaazaindenes, benzothiazoles, naphthothiazoles, benzoxazoles, naphthoxazoles, pyridines, quinolines, pyrimidines, quinoxylines, quinazolines, it being possible for these radicals in turn to be substituted, for example by alkyl, preferably up to 18 carbon atoms, aryl, such as phenyl or naphthyl, hydroxyl , Alkoxy, amino, or alkyl, acyl or aryl-substituted amino groups, mercapto, substituted mercapto groups, halogen, sulfo or carboxyl groups,

X = eine verzweigte oder unverzweigte Alkylenkette mit vorzugsweise 2 bis 12 Kohlenstoffatomen in der Kette, wobei das Alkylen substituiert sein kann mit z. B. Aryl, wie Phenyl, oder Halogen, wie Chlor.X = a branched or unbranched alkylene chain with preferably 2 to 12 carbon atoms in the chain, wherein the alkylene can be substituted with e.g. B. aryl, such as phenyl, or halogen such as chlorine.

Die Verbindungen sind lichtempfindlich und nach der Belichtung durch die gleichen Entwickler entwickelbar, die zur Reduktion von belichteten Silberhalogeniden verwendet werden.The compounds are photosensitive and after exposure to the same developer developable, which are used for the reduction of exposed silver halides.

Die erfindungsgemäßen Verbindungen stellen eine wertvolle Ergänzung der in dem Hauptpatent beschriebenen Verbindungen dar, mit dem sie im Gemisch angewendet werden können. Silbersalze, Als Erfinder benannt:The compounds according to the invention represent a valuable addition to those described in the main patent Compounds with which they can be used in a mixture. Silver salts, named as inventor:

Dr. Edith Weyde,Dr. Edith Weyde,

Dr. Anita von König, LeverkusenDr. Anita von König, Leverkusen

die im Anion einen längeren Alkylrest von 4 bis 18 C-Atomen enthalten, sind z. B. für die Wärmeentwicklung besonders geeignet. Silbersalze, die im Anion saure Gruppen, z. B. Carboxyl- oder Sulfogruppen, besitzen, sind für das Silbersalzdiffusionsverfahren oder die Fixierentwicklung besonders geeignet.which contain a longer alkyl radical of 4 to 18 carbon atoms in the anion are, for. B. for heat generation particularly suitable. Silver salts containing acidic groups in the anion, e.g. B. carboxyl or sulfo groups, are special for silver salt diffusion process or fixation development suitable.

Infolge der gegenüber den Silberhalogeniden veränderten Löslichkeitsverhältnisse ist mit diesen Verbindungen die Silbersalzdiffusion in Abwesenheit von Silbersalzlösungsmitteln, wie Thiosulfat, durchführbar. As a result of the changed solubility ratios compared to the silver halides with these compounds the silver salt diffusion is feasible in the absence of silver salt solvents such as thiosulfate.

Mit den Silbersalzen können sehr feinkörnige, stabile Emulsionen hergestellt werden. Die erfindungsgemäßen Silbersalze unterscheiden sich von den Silbersalzen der aliphatischen und aromatischen Carbonsäuren, Amino- und Hydroxycarbonsäuren dadurch, daß mit ihnen wesentlich stabilere, nicht verschleierte Emulsionen mit einer wesentlich gesteigerten Deckkraft hergestellt werden können. Die erfindungsgemäßen Silberverbindungen zeigen im allgemeinen in wäßrigem Ammoniak eine größere Löslichkeit, auf Grund deren die Verarbeitung leichter und schneller erfolgen kann, was insbesondere bei maschineller Entwicklung von erheblichem Vorteil ist.Very fine-grained, stable emulsions can be produced with the silver salts. The invention Silver salts differ from the silver salts of the aliphatic and aromatic Carboxylic acids, amino and hydroxycarboxylic acids in that they are much more stable, not fogged emulsions can be produced with a significantly increased opacity. the Silver compounds according to the invention generally show a greater value in aqueous ammonia Solubility, due to which processing can be done more easily and quickly, what in particular is of considerable advantage in machine development.

709 690/470709 690/470

Im einzelnen seien die folgenden Verbindungen angeführt:The following compounds are listed in detail:

Literaturliterature

SchmelzpunktMelting point

,CH2 — CH2 — CH2 — COOH, CH 2 - CH 2 - CH 2 - COOH

^CH2 — CH2 — CH2 — COOH^ CH 2 - CH 2 - CH 2 - COOH

S-CH2- CH2 — COOH CIS-CH 2 - CH 2 - COOH CI

S-CH2- CH2 — CH2 — COOH S-CH2- CH2 — COOHS-CH 2 - CH 2 - CH 2 - COOH S-CH 2 - CH 2 - COOH

H3C-OC-HNH 3 C-OC-HN

B e i 1 s t e i η , Bd. 3, S. 312B e i 1 s t e i η, Vol. 3, p. 312

B e i 1 s t e i η , Bd. 6, 2. Ergänzungsband, S. 293B e i 1 s t e i η, Vol. 6, 2nd supplementary volume, P. 293

B e i 1 s t e i η , Bd. 6, 2. Ergänzungsband, S. 298B e i 1 s t e i η, Vol. 6, 2nd supplementary volume, P. 298

101101

58 bis 6058 to 60

87 bis 8987 to 89

S-CH2- CH2 — COOHS-CH 2 - CH 2 - COOH

105105

114 bis 115114 to 115

122 bis 123122 to 123

135 bis 136135 to 136

pastenförmige Substanzpasty substance

129 bis 130129 to 130

Literaturliterature

SchmelzpunktMelting point

0C 0 C

CH2-CH2-COOHCH 2 -CH 2 -COOH

S-CH2-CH2 S-CH 2 -CH 2

COOHCOOH

CH2-CH2-COOHCH 2 -CH 2 -COOH

CH2 CH 2

CH3 CH 3

CH — COOHCH - COOH

li3cjPrci CH3 li3cj P rci CH 3

S — CH2 — CH — COOHS - CH 2 - CH - COOH

CH3 CH 3

CH-CH2-COOHCH-CH 2 -COOH

CH-CH2-COOHCH-CH 2 -COOH

N-NN-N

HOOC - H2C - H2C - S —( c j— S - CH2 - CH2 - COOHHOOC - H 2 C - H 2 C - S - ( c j - S - CH 2 - CH 2 - COOH

N-NN-N

N —I ο J— S — CH2 — CH2 — COOH HN - I o J - S - CH 2 - CH 2 - COOH H

-N-N

S-CH2- CH2 — CH2 — COOHS-CH 2 - CH 2 - CH 2 - COOH

B e i 1 s t e i η ,
Bd. 6,For 1 stei η,
Vol. 6,

2. Ergänzungsband.
S. 3062nd supplementary volume.
P. 306

B e i 1 s t e i η ,
Bd. 6,For 1 stei η,
Vol. 6,

2. Ergänzungsband,
S. 3132nd supplementary volume,
P. 313

145145

133133

165165

41 bis41 to

50 bis50 to

118 bis118 to

109109

146146

181 bis181 to

Die Verbindungen mit freien Mercaptogruppen 65 Die Verbindungen können nach den in den ansind, da ihre Silbersalze zum Ausflocken neigen, gegebenen Literaturstellen beschnebenen Verfahren weniger geeignet als die Verbindungen mit sub- hergestellt werden. Die übrigen Verbindungen können stituierten Mercaptogruppen. aus den entsprechenden Mercaptanen und denThe compounds with free mercapto groups 65 The compounds can be prepared by the methods described in the literature references given, since their silver salts tend to flocculate, less suitably than the compounds with sub-. The other compounds can be substituted mercapto groups. from the corresponding mercaptans and the

11

organischen Halogenverbindungen bzw. Halogencarbonsäuren in alkalischer Lösung hergestellt werden analog den im Houben — Weyl, Bd. 9, S. 103 bis 113, beschriebenen Verfahren. Die Verbindungen können als freie Säuren oder als Alkalisalze isoliert werden. Durch Umkristallisieren oder Umfällen in Wasser oder Alkohol können die Verbindungen gereinigt werden.organic halogen compounds or halocarboxylic acids are produced in alkaline solution analogous to the method described in Houben - Weyl, Vol. 9, pp. 103 to 113. The connections can be isolated as free acids or as alkali salts. By recrystallization or reprecipitation in Water or alcohol can clean the connections.

Zur Herstellung des erfindungsgemäßen photographischen Materials können die Silbersalze aus äquimolaren Mengen der die Thiocarbonsäuregruppierung enthaltenden Verbindung und einem löslichen Silbersalz, wie Silbernitrat, hergestellt werden. Die Reaktion erfolgt in wäßriger Lösung der Reaktionskomponenten, bevorzugt in Gegenwart eines filmbildenden Bindemittels, wie beispielsweise photographischer Gelatine, Polyvinylalkohol, Natriumalginat od. dgl. Je nach der angewandten Art des Thiocarbonsäurederivates ist das optimale molare Verhältnis zum Silbersalz 1 : 1 oder größer als 1:1. Es hat sich gezeigt, daß ein Uberschuß an wasserlöslichem Silbersalz Schleier in der photographischen Emulsion bildet, überschüssige Mengen an Carboxyalkylmercaptoverbindung können dagegen den Schleier verbessern, ohne die Lichtempfindlichkeit zu vermindern. Durch die Fällung des Silbersalzes in Gegenwart eines filmbildenden Bindemittels wird eine für Beschichtungszwecke geeignete Emulsion erhalten. Die Emulsionen können wie Halogensilberemulsionen gereift und zur Entfernung der wasserlöslichen Salze gewässert oder auch ungewässert verwendet werden. Den erfindungsgemäßen Emulsionen können selbstverständlich weitere in der Emulsionstechnik bekannte Zusätze, wie beispielsweise optische oder chemische Sensibilisierungsmittel, Farbstoffe, Stabilisatoren, Härtungsmittel, Netzmittel u. dgl., zugesetzt werden. For the production of the photographic material according to the invention, the silver salts can be selected from equimolar amounts of the compound containing the thiocarboxylic acid group and one soluble silver salt such as silver nitrate. The reaction takes place in an aqueous solution of the Reaction components, preferably in the presence of a film-forming binder, such as photographic gelatin, polyvinyl alcohol, sodium alginate or the like, depending on the type used of the thiocarboxylic acid derivative, the optimal molar ratio to the silver salt is 1: 1 or greater than 1: 1. It has been shown that an excess of water-soluble silver salt fog in the photographic Emulsion forms, excess amounts of carboxyalkyl mercapto compound can, however improve haze without reducing photosensitivity. Through the felling of the silver salt in the presence of a film-forming binder becomes one suitable for coating purposes Get emulsion. The emulsions can be ripened and removed for removal like silver halide emulsions of the water-soluble salts can be used with water or without water. The invention Of course, emulsions can contain other additives known in emulsion technology, such as for example, optical or chemical sensitizers, dyes, stabilizers, hardeners, wetting agents and the like can be added.

Die Emulsionen können nach bekannten Verfahren auf eine Unterlage aufgetragen werden.The emulsions can be applied to a substrate by known methods.

Zur Umsetzung mit den Carboxyalkylmercaptoverbindungen können wasserlösliche anorganische und organische Silbersalze sowie Silberkomplexe verwendet werden. Das Anion der für die Herstellung der erfindungsgemäßen Silbersalze verwendeten Silbersalze kann selbst in den photographischen Emulsionen verwendbar sein, z. B. Härtungsmittel zur Einstellung des gewünschten pH-Wertes od. dgl.Water-soluble inorganic compounds can be used for reaction with the carboxyalkyl mercapto compounds and organic silver salts and silver complexes can be used. The anion of the for making of the silver salts of the present invention can be used even in the photographic emulsions be usable, e.g. B. hardeners to adjust the desired pH or the like.

Die erfindungsgemäßen Emulsionen können auch in Mischung miteinander oder mit den üblichen Halogensilberemulsionen verwendet werden.The emulsions according to the invention can also be mixed with one another or with the usual Halogen silver emulsions can be used.

Die folgenden Beispiele sollen die Erfindung näher veranschaulichen. Die Herstellung der lichtempfindlichen Emulsionen erfolgt in der in der Emulsionstechnik üblichen Weise. The following examples are intended to illustrate the invention in more detail. The manufacture of the photosensitive Emulsions are carried out in the manner customary in emulsion technology.

Beispiel 1example 1

Zu 11 einer 8%igen wäßrigen Gelatinelösung werden bei 40°C zugesetzt:To 11 of an 8% aqueous gelatin solution are added at 40 ° C:

30 ml einer 40%igen Zitronensäurelösung, 18 g Verbindung 18, gelöst in Wasser, das erforderlichenfalls zur Erleichterung der Auflösung eine geringe Menge Natronlauge enthält.30 ml of a 40% citric acid solution, 18 g of compound 18, dissolved in water, if necessary contains a small amount of sodium hydroxide solution to facilitate dissolution.

Dann werden 100 ml einer 10%igen Silbernitratlösung unter kräftigem Rühren hinzugefügt und einige Minuten bei 40° C digeriert.Then 100 ml of a 10% silver nitrate solution are added with vigorous stirring and Digested a few minutes at 40 ° C.

484484

Nach Zusatz eines Netzmittels, z. B. von 5 ml einer 30%igen wäßrigen Saponinlösung und eines Härtungsmittels, z. B. 1 ml einer 30%igen Formaldehydlösung, wird die Emulsion in bekannter Weise auf Papier oder eine transparente Unterlage aufgetragen und getrocknet. Das beschichtete Material hat eine Empfindlichkeit wie übliche photographische Chlorsilber-Kontaktkopierpapiere. Nach der Belichtung kann wie üblich entwickelt, fixiert und gewässert werden.After adding a wetting agent, e.g. B. of 5 ml of a 30% aqueous saponin solution and one Hardening agent, e.g. B. 1 ml of a 30% formaldehyde solution, the emulsion is in a known manner applied to paper or a transparent base and dried. The coated material has the same sensitivity as conventional chlorine silver photographic contact copy papers. After Exposure can be developed, fixed and watered as usual.

Als Entwickler wird die folgende Entwicklermischung verwendet:The following developer mix is used as a developer:

1 g p-Methylaminophenol,1 g p-methylaminophenol,

13 g Natriumsulfit (sicc),
3 g Hydrochinon,13 g sodium sulfite (sicc),
3 g hydroquinone,

26 g Soda (sicc),
1 g Bromkalium,26 g soda (sicc),
1 g potassium bromide,

gelöst in 1 1 Wasser.dissolved in 1 liter of water.

Da das Silbersalz sehr feinkörnig ausfällt, kann man diese Emulsionen verhältnismäßig silberarm herstellen, ohne eine mangelnde Deckung der entwickelten Bilder befürchten zu müssen. Statt der Verbindung 18 kann man auch die folgenden Verbindungen in den angegebenen Mengen verwenden:Since the silver salt is very fine-grained, these emulsions can be relatively low in silver without worrying about insufficient coverage of the developed images. Instead of the Compound 18 one can also use the following compounds in the specified amounts:

14 g Verbindung 3,
13 g Verbindung 13,
21 g Verbindung 17,
16 g Verbindung 16,
16 g Verbindung 11.14 g compound 3,
13 g compound 13,
21 g compound 17,
16 g compound 16,
16 g compound 11.

Beispiel 2Example 2

Zu 11 einer 8%igen Gelatinelösung werden 30 ml einer 40%igen Zitronensäure zugesetzt und die Lösung auf 45 °C erwärmt. 15 g der in Wasser mit einem geringen Zusatz an Natronlauge gelösten Verbindung 1 werden hinzugefügt und dann unter kräftigem Rühren mit 100 ml einer 10%igen Silbernitratlösung gefällt. Vor dem Beguß werden 3 ml einer l%igen alkoholischen Lösung von l-Phenyl-5-mercaptotetrazol, 5 ml einer 1 %igen alkoholischen Lösung von Benztriazol, 1 ml einer 30%igen Formaldehydlösung und 5 ml 30%iges Saponin zugesetzt. Die Emulsion wird in bekannter Weise auf ein Papier aufgetragen und getrocknet.To 11 of an 8% gelatin solution, 30 ml of 40% citric acid are added and the Solution heated to 45 ° C. 15 g of the compound dissolved in water with a small amount of sodium hydroxide solution 1 are added and then with vigorous stirring with 100 ml of a 10% silver nitrate solution pleases. Before casting, 3 ml of a 1% alcoholic solution of l-phenyl-5-mercaptotetrazole, 5 ml of a 1% alcoholic solution of benzotriazole, 1 ml of a 30% formaldehyde solution and 5 ml of 30% saponin added. The emulsion is in a known manner on a Paper applied and dried.

Da das Silbersalz sich verhältnismäßig leicht in einer alkalischen Sulfitlösung löst, kann dieses Material als Negativmaterial beim Silbersalzdiffusionsverfahren ohne Anwendung von Thiosulfat dienen. Das belichtete Negativ wird in üblicher Weise unter Verwendüng von thiosulfatfreien Bildempfangsmaterialien und thiosulfatfreien Entwicklern entwickelt. Nach der Trennung der beiden Materialien wird eine gut gedeckte Kopie erhalten.Since the silver salt dissolves relatively easily in an alkaline sulfite solution, this can Material as negative material in the silver salt diffusion process without the use of thiosulphate to serve. The exposed negative is produced in the usual way using thiosulphate-free image-receiving materials and thiosulfate-free developers. After separating the two materials, a well-muted copy is obtained.

Beispiel 3Example 3

Zu 11 einer 8%igen Gelatinelösung werden 2 ml einer 40%igen Zitronensäure zugesetzt und auf 40°C erwärmt. Dann werden 15 g von in Wasser mit einem geringen Zusatz an Natronlauge gelösten Verbindung 10 hinzugefügt, und unter kräftigem Rühren wird mit 100 ml einer 10%igen Silbernitratlösung gefällt. Vor dem Beguß werden zugesetzt:2 ml of 40% citric acid are added to 11 of an 8% gelatin solution and heated to 40.degree warmed up. Then 15 g of compound dissolved in water with a small amount of sodium hydroxide solution added 10 is added, and while stirring vigorously, 100 ml of a 10% silver nitrate solution is added pleases. Before casting, the following are added:

125 g Natriumacetat (krist.),
5 g Kaliummetabisulfit,
5 g 4-diäthylaminobenzol-aminomethansulfonsaures-(l)-Natrium,
5 ml 30°/oiges Saponin.125 g sodium acetate (crystalline),
5 g potassium metabisulphite,
5 g of 4-diethylaminobenzene-aminomethanesulphonic acid (l) -sodium,
5 ml of 30% saponin.

Claims (3)

Die Emulsion wird in bekannter Weise auf ein Papier aufgetragen und getrocknet. Nach der Belichtung kann das Material durch Wärme entwickelt werden oder als Negativmaterial für das Entwicklersublimationsverfahren, z. B. nach dem in der deutsehen Auslegeschrift 1 159 758 beschriebenen, verwendet werden. Patentansprüche:The emulsion is applied to paper in a known manner and dried. After exposure, the material can be developed by heat or used as negative material for the developer sublimation process, e.g. B. after that described in the German Auslegeschrift 1 159 758, can be used. Patent claims: 1. Lichtempfindliches photographisches Material mit mindestens einer lichtempfindlichen Silbersalzemulsionsschicht gemäß Patent 1 214083, gekennzeichnet durch einen Gehalt an einem Silbersalz einer Thiocarbonsäure oder deren Derivaten, die zwischen der Carboxylgruppe und der Thiogruppierung mindestens zwei C-Atome enthält, als lichtempfindliche Verbindung. 1. Light-sensitive photographic material having at least one light-sensitive material Silver salt emulsion layer according to Patent 1,214,083, characterized by a content on a silver salt of a thiocarboxylic acid or its derivatives, which is between the carboxyl group and the thio group contains at least two carbon atoms, as a photosensitive compound. 2. Lichtempfindliches photographisches Material nach Anspruch 1, dadurch gekennzeichnet, daß in der lichtempfindlichen Schicht Silbersalze der folgenden Formel enthalten sind:2. Photosensitive photographic material according to claim 1, characterized in that that the photosensitive layer contains silver salts of the following formula: Ri — (S)n — X — COOAg
worin bedeutet:Ri - (S) n - X - COOAg
where means: η = 1 oder 2,
Ri = Wasserstoff nur bei η = 1, Alkyl, Aryl η = 1 or 2,
Ri = hydrogen only if η = 1, alkyl, aryl oder heterocyclische Ringe,
X = verzweigte oder unverzweigte Alkylengruppen mit 2 bis 12 C-Atomen.or heterocyclic rings,
X = branched or unbranched alkylene groups with 2 to 12 carbon atoms. 3. Lichtempfindliches photographisches Material nach Anspruch 1, dadurch gekennzeichnet, daß es als Bindemittel für die lichtempfindliche Schicht Gelatine enthält.3. Photosensitive photographic material according to claim 1, characterized in that that it contains gelatin as a binder for the photosensitive layer. 709 690/470 11.67 709 690/470 11.67 Q Q Bundesdruckerei BerlinBundesdruckerei Berlin
DEA48186A 1964-08-14 1965-01-21 Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer Pending DE1255484B (en)

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DEA46854A DE1214083B (en) 1964-08-14 1964-08-14 Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer
DEA48186A DE1255484B (en) 1964-08-14 1965-01-21 Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer
US472308A US3330663A (en) 1964-08-14 1965-07-15 Silver salts of sulfur-containing aliphatic carboxylic acids as lightsensitive compounds
CH1028065A CH458056A (en) 1964-08-14 1965-07-22 Photographic light sensitive material
DK416665AA DK113969B (en) 1964-08-14 1965-08-13 Photosensitive photographic material.
NL6510643A NL6510643A (en) 1964-08-14 1965-08-13
SE10616/65A SE310120B (en) 1964-08-14 1965-08-13
GB34819/65A GB1111492A (en) 1964-08-14 1965-08-13 Photographic material
FR28394A FR1443002A (en) 1964-08-14 1965-08-14 Photographic material containing silver salts of aliphatic carboxylic acids containing sulfur
AT752065A AT259366B (en) 1964-08-14 1965-08-16 Photographic material
BE668340D BE668340A (en) 1964-08-14 1965-08-17

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DEA48186A DE1255484B (en) 1964-08-14 1965-01-21 Photographic light-sensitive material comprising at least one silver salt emulsion light-sensitive layer

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DK (1) DK113969B (en)
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US4190216A (en) * 1976-05-28 1980-02-26 Agfa-Gevaert, A.G. Narrow gauge film cassette
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Publication number Priority date Publication date Assignee Title
DE2144127A1 (en) * 1971-09-03 1973-03-08 Agfa Gevaert Ag METHOD OF PRODUCING A STAIN-INSENSITIVE PHOTOGRAPHIC SILVER HALOGENIDE EMULSION
US4190216A (en) * 1976-05-28 1980-02-26 Agfa-Gevaert, A.G. Narrow gauge film cassette
EP0030632A2 (en) * 1979-12-13 1981-06-24 MERCK PATENT GmbH Benzothiazole derivatives, pharmaceutical compositions containing them and process for their preparation
EP0030632A3 (en) * 1979-12-13 1981-09-02 Merck Patent Gesellschaft Mit Beschrankter Haftung Benzothiazole derivatives, pharmaceutical compositions containing them and process for their preparation

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AT259366B (en) 1968-01-10
BE668340A (en) 1966-02-17
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